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[ CAS No. 54605-72-0 ] {[proInfo.proName]}

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Chemical Structure| 54605-72-0
Chemical Structure| 54605-72-0
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Product Details of [ 54605-72-0 ]

CAS No. :54605-72-0 MDL No. :MFCD02179568
Formula : C10H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :PHVRLPFVPVKYOI-UHFFFAOYSA-N
M.W : 172.18 Pubchem ID :952089
Synonyms :

Calculated chemistry of [ 54605-72-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.95
TPSA : 34.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 1.35
Log Po/w (WLOGP) : 1.68
Log Po/w (MLOGP) : 1.07
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : 1.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.25
Solubility : 0.963 mg/ml ; 0.0056 mol/l
Class : Soluble
Log S (Ali) : -1.68
Solubility : 3.56 mg/ml ; 0.0207 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.87
Solubility : 0.232 mg/ml ; 0.00135 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 54605-72-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 54605-72-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 54605-72-0 ]
  • Downstream synthetic route of [ 54605-72-0 ]

[ 54605-72-0 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 54605-72-0 ]
  • [ 15115-52-3 ]
Reference: [1] Pharmazie, 1986, vol. 41, # 11, p. 813 - 814
  • 2
  • [ 1126-00-7 ]
  • [ 68-12-2 ]
  • [ 54605-72-0 ]
YieldReaction ConditionsOperation in experiment
90% at 100℃; 2) The 7.3 g (0.1 µM) DMF is added to the 250 ml three-opening in the bottle, cryohydrate under bath after stirring, dropping 15.4 g (0.1 µM) phosphorus oxychloride, 1 h after dropwise 2.88 g (0.02 µM) N - phenyl pyrazole, heating up to 100 °C reflux, the reaction 3 - 6 hours, TLC monitoring after the reaction, the reaction the patient into the ice water, carbonate sodium accent to the neutral, adding (3 × 50 ml) ethyl acetate extraction, the organic phase with saturated salt water 50 ml washing, desolvation residue after column chromatography (eluting agent is ethyl acetate with petroleum ether (reflux 60 - 90 °C), the volume ratio of 1:5), shall be 3.10 g white solid, yield 90.0percent.
37%
Stage #1: at 0℃; for 1.2 h;
Stage #2: at 0 - 100℃; for 2.86667 h;
Procedure: (Vilsmeier-type formylation reaction) A 100 ml reactor, under nitrogen and with magnetic stirring, is loaded with 10 ml of DMF which are immediately cooled to 0° C. by means of an ice/water bath. The phosphorus oxychloride is added dropwise, by means of a syringe, in 12 minutes. After 1 hour at 0° C., a solution of 1-phenylpyrazole (in 10 ml of DMF) is added in 2 minutes by means of a syringe, by rapidly running it in dropwise. After a further 5 minutes at 0° C., the mixture is brought back to ambient temperature for 15 minutes and then placed at 100° C. for 2 h 30 min. Complete disappearance of the starting product is observed by TLC (9/1 hexane/acetic acid (EtOAc): Rf: 0.35). Once it has returned to ambient temperature, the reaction medium is carefully added to 20 g of ice-cold water, under a hood. After stirring for 18 hours, the mixture is extracted twice with 250 ml of ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered through a sintered glass filter, and evaporated to dryness, and the residue is then filtered through a patch of silica on a sintered glass filter (elution: pure hexane, 8/2 hexane/CH2Cl2, 1/1 hexane/CH2Cl2, 100percent CH2Cl2). The purely chlorinated fractions make it possible to isolate 1.17 g of a yellow oil, which crystallizes spontaneously once taken up in hexane. A second fraction (eluted with 1/1 hexane/CH2Cl2) taken up with hexane also makes it possible to isolate a solid. The solids are combined and washed three times with 10 ml of hexane so as to obtain 2.21 g of a white solid (yield 37percent).
Reference: [1] Patent: CN107964007, 2018, A, . Location in patent: Paragraph 0498
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 1, p. 295 - 302
[3] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 4, p. 957 - 960
[4] Patent: US2006/34786, 2006, A1, . Location in patent: Page/Page column 62
[5] Synthetic Communications, 1998, vol. 28, # 7, p. 1299 - 1321
[6] Tetrahedron, 2001, vol. 57, # 20, p. 4397 - 4403
[7] Patent: US2009/239810, 2009, A1, . Location in patent: Page/Page column 72
  • 3
  • [ 100-97-0 ]
  • [ 1126-00-7 ]
  • [ 54605-72-0 ]
Reference: [1] Synthetic Communications, 2013, vol. 43, # 12, p. 1633 - 1639
[2] Chemical Biology and Drug Design, 2017, vol. 90, # 3, p. 432 - 442
[3] Inflammopharmacology, 2018, vol. 26, # 1, p. 217 - 226
[4] Life Sciences, 2012, vol. 90, # 23-24, p. 910 - 916
  • 4
  • [ 1126-00-7 ]
  • [ 497-19-8 ]
  • [ 54605-72-0 ]
Reference: [1] Journal of the Brazilian Chemical Society, 2011, vol. 22, # 2, p. 352 - 358
  • 5
  • [ 130161-49-8 ]
  • [ 54605-72-0 ]
Reference: [1] Heterocycles, 1990, vol. 31, # 6, p. 1105 - 1109
[2] Bulletin de la Societe Chimique de France, 1990, # 5, p. 660 - 666
  • 6
  • [ 130161-47-6 ]
  • [ 54605-72-0 ]
Reference: [1] Heterocycles, 1990, vol. 31, # 6, p. 1105 - 1109
[2] Bulletin de la Societe Chimique de France, 1990, # 5, p. 660 - 666
  • 7
  • [ 18655-47-5 ]
  • [ 100-63-0 ]
  • [ 54605-72-0 ]
Reference: [1] Heterocycles, 1990, vol. 31, # 6, p. 1105 - 1109
[2] Bulletin de la Societe Chimique de France, 1990, # 5, p. 660 - 666
  • 8
  • [ 1126-00-7 ]
  • [ 76-05-1 ]
  • [ 54605-72-0 ]
YieldReaction ConditionsOperation in experiment
0.72 g Inert atmosphere; Reflux A solution of 1-phenylpyrazole (2.0g, 13.87 mmoles) in TFA (l7mL) was stirred under a nitrogen atmosphere and treated with. hexamethylene tetramine (2.92 g, 20.81 mmoles). The reaction was refluxed overnight, and then cooled and poured into saturated sodium bicarbonate aqueous solution to adjust the pH to 7. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with brine, dried overMgSO4, filtered and concentrated to 2.78 g of crude oil. Flash column chromatography on silica gel with a 40 gram Isco MPLC column using 10-20percent EtOAc-Hexanes gradient provided 0.72 g of the title compound.1H NMR ö 9.98 (s, 1H), 8.44(s, 1H), 8.17 (s, 1H), 7.70 (m, 2H), 7.5 (m,2H), 7.4 (m,1H).
Reference: [1] Patent: WO2015/89003, 2015, A1, . Location in patent: Page/Page column 44
  • 9
  • [ 100-63-0 ]
  • [ 54605-72-0 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1990, # 5, p. 660 - 666
[2] Heterocycles, 1990, vol. 31, # 6, p. 1105 - 1109
[3] Journal of the Chemical Society, 1954, p. 2293,2295
  • 10
  • [ 27935-60-0 ]
  • [ 68-12-2 ]
  • [ 54605-72-0 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 9, p. 1242 - 1243
  • 11
  • [ 130161-48-7 ]
  • [ 54605-72-0 ]
Reference: [1] Heterocycles, 1990, vol. 31, # 6, p. 1105 - 1109
[2] Bulletin de la Societe Chimique de France, 1990, # 5, p. 660 - 666
[3] Heterocycles, 1990, vol. 31, # 6, p. 1105 - 1109
  • 12
  • [ 57023-37-7 ]
  • [ 54605-72-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 4, p. 1265 - 1269
[2] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 4, p. 1265 - 1269
  • 13
  • [ 60441-21-6 ]
  • [ 54605-72-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 4, p. 1265 - 1269
[2] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 4, p. 1265 - 1269
  • 14
  • [ 59-88-1 ]
  • [ 54605-72-0 ]
Reference: [1] Chemical Biology and Drug Design, 2017, vol. 90, # 3, p. 432 - 442
[2] Inflammopharmacology, 2018, vol. 26, # 1, p. 217 - 226
  • 15
  • [ 2600-63-7 ]
  • [ 54605-72-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 4, p. 1265 - 1269
  • 16
  • [ 75594-89-7 ]
  • [ 54605-72-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 4, p. 1265 - 1269
  • 17
  • [ 35715-71-0 ]
  • [ 54605-72-0 ]
Reference: [1] Journal of the Chemical Society, 1954, p. 2293,2295
  • 18
  • [ 1126-00-7 ]
  • [ 54605-72-0 ]
Reference: [1] Journal of the Chemical Society, 1954, p. 2293,2295
  • 19
  • [ 100-97-0 ]
  • [ 100-63-0 ]
  • [ 54605-72-0 ]
Reference: [1] Magnetic Resonance in Chemistry, 2011, vol. 49, # 8, p. 537 - 542
  • 20
  • [ 54605-72-0 ]
  • [ 1134-50-5 ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydroxide; dihydrogen peroxide In water at 45 - 50℃; Procedure: The sodium hydroxide is dissolved in 20 ml of water in a 100 ml three-necked reactor under nitrogen and with magnetic stirring. The pyrazole is then added in a single step. A persistent insoluble product is observed, even at a temperature of 45-50° C. The hydrogen peroxide is added to the suspension in 6 portions over 50 minutes. After 5 hours at 50° C., TLC monitoring makes it possible to observe that a substantial part of the substrate remains. 10 ml of 1N NaOH (0.4 g of NaOH) and 5 g of aqueous hydrogen peroxide are added. After stirring for a further hour at 50° C., the insoluble product has completely disappeared and TLC monitoring makes it possible to observe that the starting product has been entirely consumed (visualization: dinitrophenylhydrazine). The reaction medium brought back to ambient temperature is then added to 150 ml of an ice/2N HCl mixture (2/1). The white precipitate formed is filtered through a Buchner funnel after stirring for 30 minutes and washed 3 times with water. After having been resolubilized in 250 ml of ethyl acetate, dried over MgSO4 and then filtered and evaporated to dryness, 2.25 g of a white product are thus isolated (yield: 96percent).
Reference: [1] Inflammopharmacology, 2018, vol. 26, # 1, p. 217 - 226
[2] Patent: US2006/34786, 2006, A1, . Location in patent: Page/Page column 62-63
[3] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 4, p. 1265 - 1269
[4] Patent: US2009/239810, 2009, A1, . Location in patent: Page/Page column 72
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